5-bromo-2-(4-methyl-1H-imidazol-1-yl)benzonitrile → HCID 67548883, compound

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Reaction Steps

A solution of 5-bromo-2-(4-methyl-imidazol-1-yl)-benzonitrile (11.0 g, 42.0 mmol) and N,N-dimethylmethyleneiminium chloride (5.0 g, 53.4 mmol) in DMF (75 mL) was stirred at 90° C. for 16 h. The solvent was evaporated and the oily residue was partitioned between saturated aqueous sodium bicarbonate solution and ethyl acetate. The organic phase was dried over sodium sulfate, concentrated and chromatographed (SiO2, dichloromethane:methanol=1000:0 to 965:35) to afford the title compound as an oil that solidifies on standing (10.62 g, 79%). MS: m/e=321.3/319.2 [M+H]+.

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